Halakhic Approach
Soloveitchik was known for his stringency in halakha. This partly stems from his use of the Brisker method of study, in which laws are broken down into precise components, which can then be assembled into new combinations, creating novel halachic possibilities which perhaps a person should be strict to follow or avoid. This, however, does not explain all of his stringencies.
For example, he is reputed to have observed a "second day" of Yom Tov in his home in Jerusalem. Normally, this second day is observed outside the Holy Land, in memory of ancient times, when people far from Jerusalem would not hear about the declaration of the new month and would not know on which day to celebrate holidays. However, the Brisker Rov worried that while the messengers announcing the new month traveled from Jerusalem to the outskirts of the Holy Land, they may not have passed by the exact place where he lived. Taking this possibility into account, he observed a second day of Yom Tov, just to be safe.
However, in one case the Brisker Rov surprised observers by not following a well-known stringency. Halakha says that on Sukkot, one is required to eat certain foods in a sukkah, and it is praiseworthy but not required that all eating and drinking to take place in the sukkah. However, the Brisker Rov was willing to eat and drink these foods outside the sukkah.
Read more about this topic: Yitzchok Zev Soloveitchik
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